Underseeding red clover in winter wheat is a beneficial agronomic practice. Still, many growers tend to forgo this approach. One reason is that herbicides used on winter wheat may injure underseeded red clover, reducing its biomass and the subsequent benefits it provides. Therefore, the effect of winter wheat herbicides on underseeded red clover needs to be evaluated. The objectives of this research were to assess the crop tolerance of underseeded red clover to ten winter wheat herbicides used in Ontario, Canada and determine if red clover tolerance differed when the herbicides were applied at various winter wheat growth stages. Experiments were conducted in 2009 and 2010 at four different Ontario locations. Each herbicide treatment was either applied at an early, normal or late timing. Overall, red clover was not affected by herbicides applied at the early timing. The likelihood of herbicides causing injury and reducing biomass of underseeded red clover increased when they were applied at the more advanced winter wheat growth stages. If timing is a constraint, the three herbicides bromoxynil/MCPA, tralkoxydim, and fenoxaprop-pethyl are the safest to use on red clover underseeded to winter wheat. The remaining herbicides 2,4-D, dicamba/MCPA/mecoprop, dichlorprop/2,4-D, thifensulfuron/ tribenuron + MCPA, fluroxypyr + MCPA, pyrasulfotole/bromoxynil, and prosulfuron + bromoxynil are more injurious, with the last two being the most harmful. By having identified the least damaging herbicides on underseeded red clover in winter wheat and the optimal timing for herbicide application, growers are more likely to adopt this beneficial agronomic practice, save on fertilizer costs and improve soil quality.